4-[1-(6,7-Dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl) piperidin-4-ylamino]benzoic acid tert-butyl ester → 4-[1-(6,7-Dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)piperidin-4-ylamino]benzoic acid
Reaction equation
C([O:5][C:6](=[O:35])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[NH:29][C:28](=[O:30])[C:27]4[C:22](=[CH:23][C:24]([O:33][CH3:34])=[C:25]([O:31][CH3:32])[CH:26]=4)[N:21]=3)[CH2:16][CH2:15]2)=[CH:9][CH:8]=1)(C)(C)C>FC(F)(F)C(O)=O>[CH3:32][O:31][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:33][CH3:34])[N:21]=[C:20]([N:17]1[CH2:18][CH2:19][CH:14]([NH:13][C:10]3[CH:11]=[CH:12][C:7]([C:6]([OH:35])=[O:5])=[CH:8][CH:9]=3)[CH2:15][CH2:16]1)[NH:29][C:28]2=[O:30]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of (15) (0.036 g, 0.074 mmol) in trifluoroacetic acid (5 mL) was capped with a drying tube and stirred at 25° C. for 12 h. The reaction mixture was evaporated to a light brown oily residue (0.059 g, quantitative yield); 1H NMR (DMSO) δ 8.00 (br s, 1H), 7.67 (d, 2H, J=8.3), 7.31 (s, 1H), 6.98 (s, 1H), 6.63 (d, 2H, J=8.2), 6.12 (br s, 1H), 4.22 (d, 2H, J=12.8), 3.86 (s, 3H), 3.81 (s, 3H), 3.65 (m, 1H), 3.28 (m, 2H), 2.03 (m, 2H), 1.49 (m, 2H); 13C NMR (DMSO) δ 167.5, 161.8, 160.7, 155.2, 151.4, 149.6, 146.3, 131.2, 124.2, 123.9, 116.9, 111.2, 108.2, 105.8, 55.8, 55.7, 47.9, 44.6, 30.8; HRMS (FAB) m/z 425.1818 (M+H)+ (C22H24N4O5 requires 425.1819); Anal. (C22H24N4O5 ·2CF3COOH·1CH3OH) C, H, N.
Sources & evidence
- ORD record
- ord-3dc2b4aedc56487ba9bbb53a82237dac
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06156758
Reaction notes
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